Radiation-sensitive resin composition

ABSTRACT

A radiation sensitive resin composition containing an alkali-soluble resin, for example a novolak-quinonediazide positive-working radiation sensitive resin composition and a chemically amplified negative-working resin composition, wherein the alkali-soluble resin contains at least an alkali-soluble resin obtained by polycondensation of a compound represented by the following general formula (I) and a phenol if necessary, with an aldehyde.                    
     wherein R represents a hydroxyl group or an alkyl group with 1 to 4 carbon atoms, n is 0 or an integer of 1 to 3 and, when n is 2 or 3, each R group may be the same or different.

This is a divisional of Ser. No. 09/600,052 filed Oct. 12, 2000, nowU.S. Pat. No. 6,342,542, which is a 371 of PCT/JP99/06074 filed Nov. 1,1999.

TECHNICAL FIELD

This invention relates to a radiation-sensitive resin composition formanufacture of semiconductor devices or liquid crystal display devices,more particularly, to a radiation-sensitive resin composition formanufacture of semiconductor devices or liquid crystal display devices,which can form a good pattern, shows excellent adhesion to a substrateand yet can be easily removed with a remover.

BACKGROUND ART

In a process for manufacturing semiconductor devices such as IC or LSIor liquid crystal displays, fine patterns have been formed by forming aphotoresist layer on a silicon substrate, a substrate having a metallayer such as aluminum, molybdenum, chromium, etc. or a substrate havinga metal oxide layer such as ITO (indium tin oxide), irradiating thisphotoresist layer through a mask pattern with UV light or the like, thendeveloping it, and etching the substrate using the resulting photoresistpattern as the mask.

Various radiation-sensitive resin compositions have conventionally beenproposed which are used in such photolithography. Examples of suchcompositions include the positive-working radiation-sensitivecomposition wherein an alkali-soluble novolak resin is combined with aradiation-sensitive component of quinonediazide group-containingcompound (Japanese Unexamined Patent Publication No. H07-120914) and thenegative-working radiation-sensitive composition wherein analkali-soluble novolak resin, a cross-linking agent of alkoxymethylatedmelamine, and an acid generating agent of halogenated triazine arecombined with each other (Japanese Unexamined Patent Publication No.H05-303196).

Accurate etching of the substrate with the aid of photoresist requiresgood adhesion between the resist pattern and the substrate. To improvethe adhesion between the resist pattern and the substrate, so-calledpost-baking has been processwise proposed which comprises baking(heat-treating) the photoresist pattern obtained by the development. Asan approach of using materials, it has been proposed to add anadhesion-improving agent to the radiation-sensitive resin composition.For example, an adhesion-improving agent such as a benzimidazole, apolybenzimidazole or the like is incorporated in a positive-workingphotoresist (Japanese Unexamined Patent Publication No. H06-27657) and abenzotriazole is incorporated in a negative-working photoresist(Japanese Unexamined Patent Publication No. H08-339087).

However, as is well known, if post-baking is conducted in order toimprove adhesion between the resist and the substrate, subsequentremoval of the photoresist becomes difficult particularly with anegative-working photoresist. Further, a positive-working resist isremoved generally through dissolution in a remover, whereas anegative-working photoresist is usually swollen and not dissolved, andis removed by peeling. In the case of peeling off the photoresist,however, there arises the problem that the peeled photoresist pieces mayagain deposit on the substrate to cause pattern defects. Still further,a substrate with an ITO layer absorbs basic components such as amine,etc. in the air which inactivates an acid once generated by lightexposure in the photoresist, thus causing a problem of pattern bite intothe interface between the photoresist and the substrate. Under suchcircumstances, there has been demanded a photoresist which can form agood resist pattern, good adhesion to a substrate, and enough highremovability to be easily dissolved in a remover or the like.

Therefore, an object of the present invention is to provide a negative-or positive-working radiation-sensitive resin composition containing analkali-soluble resin which composition can form an undercut- orfooting-free excellent resist pattern on a silicon substrate, asubstrate having a metal layer or a substrate having a metal oxidelayer, which can, even after subjected to heat-treating afterdevelopment for the purpose of improving adhesion, be easily dissolvedin and removed with a remover.

DISCLOSURE OF THE INVENTION

As a result of intensive investigations, the inventors have found thatthe above-described object can be achieved by incorporating, in aradiation-sensitive resin composition containing an alkali-soluble resincomposition, an alkali-soluble resin obtained by using the compoundrepresented by the following general formula (I) as one monomercomponent (hereinafter also referred to as “aniline modified resin”) asthe alkali-soluble resin, thus having completed the present inventionbased on the finding.

That is, the present invention is a radiation-sensitive resincomposition containing an alkali-soluble resin, wherein saidalkali-soluble resin contains at least an alkali-soluble resinsynthesized using as a monomer component a compound represented by thefollowing general formula (I):

wherein R represents a hydroxyl group or an alkyl group with 1 to 4carbon atoms, n is 0 or an integer of 1 to 3 and, when n is 2 or 3, eachR group may be the same or different.

As the aniline modified resins to be used in the present invention,those which are obtained by polycondensation of the compound representedby the above general formula (I) and a phenol with an aldehyde such asformalin are most preferred. The present invention will therefore bedescribed in more detail by reference to a radiation-sensitive resincomposition containing the aniline modified resin obtained by suchpolycondensation.

As the compounds of the general formula (I) to be used as a monomercomponent constituting the aniline modified resin, there are illustratedaniline, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,5-dimethylaniline,2,6-dimethylaniline, 3,4-dimethylaniline, 3,5-dimethylaniline,2,6-diethylaniline, 2,6-diisopropylaniline, 3,5-di-tert-butylaniline,2,4,6-trimethylaniline, 2,4,6-tri-tert-butylaniline, etc. Thesecompounds may be used alone or as a mixture of two or more thereof.

As the phenols to be used as a starting material of the above-describedpolycondensation resin, any of those may be used which haveconventionally been used for forming alkali-soluble resins. Specificexamples of such phenols include phenol, p-cresol, m-cresol, o-cresol,2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol,2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol,2,3,4-trimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol,2,4,5-trimethylphenol, methylenebisphenol, methylenebis-p-cresol,resorcinol, catechol, 2-methylresorcinol, 4-methylresorcinol,o-chlorophenol, m-chlorophenol, p-chlorophenol, 2,3-dichlorophenol,m-methoxyphenol, p-methoxyphenol, p-butoxyphenol, o-ethylphenol,m-ethylphenol, p-ethylphenol, 2,3-diethylphenol, 2,5-diethylphenol,p-isopropylphenol, α-naphthol, β-naphthol, etc. These compounds may beused alone or in combination of two or more thereof.

As the aldehydes, paraformaldehyde, acetaldehyde, benzaldehyde,hydroxybenzaldehyde, chloroacetaldehyde, etc. may be used, as well asformalin, alone or as a mixture of two or more thereof.

The aniline modified polycondensation resin to be used in the presentinvention may readily be obtained in the same manner as with knownnovolak phenol resins, i.e., by heating the phenol compound and thealdehyde compound in the presence of an acid catalyst to react.Specifically, the aniline modified resin in accordance with the presentinvention is produced by mixing, with 100 parts by weight of the phenolcompound, usually 0.1-60 parts by weight of the compound represented bythe general formula (I), 10-20 parts by weight of the aldehyde compoundand 1-3 parts by weight of oxalic acid, and conducting the reaction at areaction temperature of 85-95° C. for at least 4 hours.

The aniline modified resin in accordance with the present invention hasa weight average molecular weight of 500-10,000, preferably 1,000-5,000.

The thus obtained aniline modified resin may be used alone or incombination with a conventionally known, aniline unmodifiedalkali-soluble resin or resins. As the known alkali-soluble resinsusable in combination with the aniline modified resin, those novolakresins are preferred which are obtained by polycondensation between atleast one of the above-described phenol compounds and at least one ofthe aldehyde compounds. A preferable content of the compound of formula(I) in the total alkali-soluble resin is preferably 0.1 to 40% byweight, more preferably 1 to 30% by weight.

The radiation-sensitive resin composition of the present inventioncontaining the aniline modified resin may be of positive-working type ornegative-working type. Typical examples of the positive-workingradiation-sensitive resin composition are so-calledquinonediazide-novolak type radiation-sensitive resin compositionswherein a quinonediazide group-containing compound is incorporated as aradiation-sensitive agent. In this quinonediazide-novolak typeradiation-sensitive resin composition, the above-described anilinemodified resin obtained by polycondensation and, if necessary, a knownalkali-soluble resin or resins such as novolak resins used inquinonediazide-novolak resists are used as the alkali-soluble resin.

As the quinonediazide group-containing, radiation-sensitive agents, anyof those known radiation-sensitive agents may be used that haveconventionally been used in quinonediazide-novolak resists. Preferableradiation-sensitive agents are those which are obtained by reactingnaphthoquinonediazidesulfonyl chloride or benzoquinonediazidesulfonylchloride with a low-molecular or high-molecular compound having afunctional group or groups capable of undergoing condensation reactionwith the acid chloride. As the functional group capable of undergoingcondensation reaction with acid chloride, there are illustrated ahydroxyl group and an amino group, with hydroxyl group being preferredespecially. Examples of the compound capable of undergoing condensationreaction with an acid containing a hydroxyl group include hydroquinone;resorcinol; hydroxybenzophenones such as 2,4-dihydroxybenzophenone,2,3,4-trihydroxybenzophenone, 2,4,6-trihydroxybenzophenone,2,4,4′-trihydroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone,2,2′,4,4′-tetrahydroxybenzophenone,2,2′,3,4,6′-pentahydroxybenzophenone, etc.; hydroxyphenylalkanes such asbis(2,4-dihydroxyphenyl)methane, bis(2,3,4-trihydroxyphenyl)methane,bis(2,4-dihydroxyphenyl)propane, etc.; hydroxytriphenylmethanes such as4,4′,3″,4″-tetrahydroxy-3,5,3′,5′-tetramethyltriphenylmethane,4,4′,2″,3″,4″-pentahydroxy-3,5,3′,5′-tetramethyltriphenyl-methane, etc.;and the like. These may be used alone or in combination of two or morethereof.

The quinonediazide group-containing, radiation-sensitive agent isincorporated in an amount of usually 5 to 50 parts by weight, preferably10 to 40 parts by weight, per 100 parts by weight of the alkali-solubleresin.

Typical examples of the negative-working radiation-sensitive resincomposition of the present invention are ternary chemically amplifiednegative-working resists which comprise an alkali-soluble base resin, across-linking agent and an acid-generating agent.

As the alkali-soluble base resin, the above-described aniline modifiedresins obtained by polycondensation and optionally those which have sofar been used as alkali-soluble base resins in ternary chemicallyamplified negative-working resists, such as novolak resins, are used.

As the cross-linking agent for the chemically amplified negative-workingresists, any of those may be used which have so far been used ascross-linking agents for chemically amplified negative-working resists.Preferable examples of the cross-linking agents include alkoxyalkylatedamino resins such as alkoxyalkylated melamine resins, alkoxyalkylatedbenzoguanamine resins, alkoxyalkylated urea resins, etc. as wellasmelamine type, guanamine type and urea type low-molecular derivatives.Specific examples of such alkoxyalkylated amino resins includemethoxymethylated melamine resin, ethoxymethylated melamine resin,propoxymethylated melamine resin, butoxymethylated melamine resin,ethoxymethylated benzoguanamine resin, methoxymethylated urea resin,ethoxymethylated urea resin, propoxymethylated urea resin,butoxymethylated urea resin, etc. Examples of the melamine type,guanamine type and urea type low-molecular derivatives includemethoxymethylated melamine, ethoxymethylated melamine, propoxymethylatedmelamine, butoxymethylated melamine, hexamethylol melamine,acetoguanamine, benzoguanamine, methylated benzoguanamine, monomethylolurea, dimethylol urea, etc. Of these, melamine type and benzoguanaminetype low-molecular derivatives, alkoxyalkylated benzoguanamine resinsand alkoxyalkylated melamine resins are preferred.

These cross-linking agents may be used alone or in combination of two ormore thereof, and are incorporated in an amount of usually 2 to 50 partsby weight, preferably 5 to 30 parts by weight, per 100 parts by weightof the alkali-soluble resin.

As the acid-generating agents, there are illustrated onium salts such asiodonium salts, sulfonium salts, diazonium salts, ammonium salts,pyridinium salts, etc.; halogen-containing compounds such as haloalkylgroup-containing hydrocarbon compounds, haloalkyl group-containingheterocyclic compounds, etc.; diazoketone compounds such as 1,3-diketo-2-diazo compounds, diazobenzoquinone compounds,diazonaphthoquinone compounds, etc.; sulfone compounds such asβ-ketosulfon, β-sulfonylsulfone, etc.; sulfonic acid compounds such asalkylsulfonic acid esters, haloalkylsulfonic acid esters, arylsulfonicacid esters, iminosulfonates, etc.; and the like. These acid-generatingagents may be used alone or in combination of two or more thereof, andare incorporated in an amount of usually 0.1 to 10 parts by weight,preferably 0.5 to 5.0 parts by weight, per 100 parts by weight of thealkali-soluble resin.

Further, it is preferable to incorporate a basic compound as an additivein the chemically amplified negative-working resists. This basiccompound functions to control diffusion, in the resist layer, of theacid generated from the acid-generating agent upon exposure to therebyimprove resolution or exposure latitude. Such basic compounds includeprimary, secondary or tertiary aliphatic amines, aromatic amines,heterocyclic amines, nitrogen compounds containing an alkyl group, anaryl group, etc., compounds containing an amido group or an imido group,and the like.

As the solvent for dissolving the positive-working or negative-workingradiation-sensitive resin composition of the present invention, thereare illustrated ethylene glycol monoalkyl ethers such as ethylene glycolmonomethyl ether, ethylene glycol monoethyl ether, etc.; ethylene glycolmonoalkyl ether acetates such as ethylene glycol monomethyl etheracetate, ethylene glycol monoethyl ether acetate, etc.; propylene glycolmonoalkyl ethers such as propylene glycol monomethyl ether, propyleneglycol monoethyl ether, etc.; propylene glycol monoalkyl ether acetatessuch as propylene glycol monomethyl ether acetate, propylene glycolmonoethyl ether acetate, etc.; lactic esters such as methyl lactate,ethyl lactate, etc.; aromatic hydrocarbons such as toluene, xylene,etc.; ketones such as methyl ethyl ketone, 2-heptanone, cyclohexanone,etc.; amides such as N,N-dimethylacetamide, N-methylpyrrolidone, etc.;lactones such as γ-butyrolactone, etc.; and the like. These solvents maybe used alone or in combination of two or more thereof.

In the radiation-sensitive resin composition of the present inventionmay be incorporated, if necessary, dyes, adhesion aids, surfactants,etc. Examples of the dyes include Methyl Violet, Crystal Violet,Malachite Green, etc., examples of the adhesion aids includealkylimidazolines, butyric acid, alkyl acids, polyhydroxystyrene,polyvinyl methyl ether, t-butylnovolak, epoxysilane, epoxy polymers,silanes, etc., and examples of the surfactants include nonionicsurfactants such as polyglycols and the derivatives thereof, i.e.,polypropylene glycol or polyoxyethylene lauryl ether, etc.;fluorine-containing surfactants such as Fluorad (trade name; product ofSumitomo 3M Co., Ltd.), Megafac (trade name; product of Dai-nippon Ink &Chemicals, Inc.), Surflon (trade name; product of Asahi Glass Company,Ltd.) and organosiloxane surfactants such as KP341 (trade name; productof Shin-Etsu Chemical Co., Ltd).

Best mode for Practicing the Invention

The present invention will now be described more specifically byreference to Examples which, however, are not to be construed to limitthe present invention in any way.

SYNTHESIS EXAMPLE 1 Synthesis of Aniline Modified Resin A

20 Parts by weight of aniline, 45 parts by weight of 37 wt %formaldehyde, and 1.8 parts by weight of oxalic acid were charged per100 parts by weight of a cresol mixture (m-cresol/p-cresol=6/4), and thereaction was conducted at a reaction temperature of 90° C. for 4 hours.This aniline modified resin A had amolecular weight of 1,800 asdetermined using polystyrene standards.

SYNTHESIS EXAMPLE 2 Synthesis of Aniline Modified Resin B

Aniline modified resin B was obtained in the same manner as in SynthesisExample 1 except for using 100 parts by weight of o-cresol in place of100 parts by weight of the cresol mixture.

EXAMPLES 1-3

m- and p-cresol novolak resin (m-cresol/p-cresol=6/4; weight-averagemolecular weight: 10,000 as determined using polystyrene standards),2,3,4-trihydroxybenzophenone-o-naphthoquinone-1,2-diazido-sulfonic acidtriester as a radiation-sensitive agent, and the aniline modified resinA obtained in Synthesis Example 1 were dissolved in propylene glycolmonomethyl ether acetate in aproportion (by weight) given in Table 1,and the resulting solution was filtered through a Teflon®-made 0.2 μmmembrane filter to prepare positive-working radiation-sensitivecompositions of the present invention.

Each of the compositions was spin-coated on a 4-inch silicon waferhaving thereon an ITO layer, and baked at 100° C. for 90 seconds on ahot plate to obtain a 1.5 μm-thick resist coating. This resist coatingwas exposed using a g-line stepper made by GCA Co. (DSW6400, NA=0.42),followed by developing in a 0.9 wt % potassium hydroxide aqueoussolution for 60 seconds to form a pattern. Etching was conducted with amixed solution of hydrochloric acid and ferric chloride using the thusformed patterns as a mask to thereby form, on a silicon wafer, a patternof ITO with the resist thereon. Etching time was determined so thatresist-free ITO layer on the substrate was completely etched off uponbeing dipped in an etching solution, that is, just etching period. Afterthe etching procedure, pattern form of a 5 μm-line pattern was observedunder a scanning electron microscope (SEM).

In general, post-baking after development serves to improve adhesion tothe substrate. Hence, post-baking was additionally conducted at 130° C.for 3 minutes after development and before etching, followed by the sameetching procedure in the same manner as described above, and patternform of the resulting line patterns was also observed under SEM. Resultsthus obtained are tabulated in Table 1. It can be seen from Table 1,that addition of the aniline modified resin serves to reduce or almostprevent undercut even without conducting post-baking and thatpost-baking, when conducted, ensures to completely prevent undercut.

Comparative Example 1

Procedures in Example 1 were repeated except for not adding the anilinemodified resin and pattern form was observed after etching procedure.Results thus obtained are shown in Table 1. A serious undercut wasobserved when post-baking was not conducted after development. In thecase of conducting post-baking after development, too, undercut was notcompletely prevented, though reduced to some extent.

TABLE 1 Form of Line Form of Line Novolak Resin/ Aniline Pattern PatternRadiation- Modified (without post- (with post- sensitive Agent Resin Abaking) baking) Example 1 100/15  5 Δ ◯ Example 2 100/15 10 ◯ ◯ Example3 100/15 15 ◯ ◯ Comparative 100/15  0 X Δ Example 1 ◯: with almost noundercut Δ: with reduced undercut X: with undercut

EXAMPLES 4-6

Patterns were formed in the same manner as in Examples 1-3 using thephotoresist compositions obtained in Examples 1 to 3. After formation ofthe patterns, etching was conducted in the same manner as in Examples 1to 3 using each pattern as a mask. Then, the resists were removedaccording to a dipping method at 35° C. for 300 seconds using Remover100 (made by Clariant Japan K.K.) as a remover. Separately, post-bakingwas additionally conducted at 130, 150 and 170° C., respectively, eachfor 5 minutes before the same resist-removing treatment. Results thusobtained are tabulated in Table 2. Resist coatings were removed bydissolution in the both cases of removing the resist without conductingpost-baking and removing the resist with conducting post-baking at 130,150 or 170° C. for 5 minutes after conducting development.

Comparative Example 2

A radiation-sensitive resin composition was prepared in the same manneras in Comparative Example 1, and pattern formation was conducted in thesame manner. Results obtained by conducting etching and resist-removingtreatment without post-baking and results obtained by conducting etchingand resist-removing treatment after post-baking at 130, 150 or 170° C.in the same manner as in Example 4 are shown in Table 2. In case wherepost-baking was additionally conducted, the resists were not removedwithin a predetermined period of time whereas, where removing treatmentwas conducted for a longer time, the resists were removed not bydissolution but by peeling.

TABLE 2 Novolak Resin /Radiation- Aniline Modified Without Post-sensitive Agent Resin baking 130° C. 150° C. 170° C. Example 4 100/15 5◯ ◯ ◯ X Example 5 100/15 10 ◯ ◯ ◯ ◯ Example 6 100/15 15 ◯ ◯ ◯ ◯Comparative 100/15 0 ◯ X X X Example 2 ◯: removable by dissolution X:impossible to be removed by dissolution

EXAMPLE 7

m-, p-Cresol novolak resin 100 parts by weight (m-cresol/p-cresol = 6/4;weight average molecular weight as determined using polystyrenestandards: 4,000) Ethoxymethylated benzoguanamine 25 parts by weightresin 2,4,6-Tris(trichloromethyl)- 3 parts by weight triazine Anilinemodified resin A obtained 20 parts by weight in Synthesis Example 1Tetrabutylammonium hydroxide 0.5 part by weight

The above-described components were dissolved in propylene glycolmonomethyl ether acetate, and filtered through a Teflon-made, 0.2 μmmembrane filter to prepare a negative-working radiation-sensitivecomposition.

This composition was spin-coated on a 4-inch silicon wafer havingthereon an ITO layer, and baked at 100° C. for 90 seconds on a hot plateto obtain a 1.5 μm-thick resist coating. This resist coating was exposedusing a g-line stepper made by GCA Co. (DSW6400, NA=0.42) and wassubjected to post-exposure baking (PEB) at 130° C. for 90 seconds,followed by developing in a 2.38 wt % tetramethylammonium hydroxideaqueous solution for 60 seconds to form a pattern. Etching was conductedwith a mixed solution of hydrochloric acid and ferric chloride using thethus formed patterns as a mask to thereby form, on a silicon wafer, apattern of ITO with the resist thereon. Observation of the 5 μm linepattern under a scanning type electron microscope (SEM) before and afterthe etching revealed formation of good patterns with almost no undercut.In the case of conducting post-baking treatment at 140° C. for 3 minutesafter development, better patterns were observed.

Next, patterns formed were subjected to the treatment of removing theresist according to a dipping method at 23° C. for 60 seconds usingRemover 100 (made by Clariant Japan K.K.) as a remover, thus the resistbeing removed by dissolution. In the case of similar removal of theresist after additionally conducting post-baking at 140° C. for 3minutes after the development, the resist coating was also removed bydissolution.

EXAMPLE 8

A radiation-sensitive resin composition was prepared in the same manneras in Example 7 except for using the aniline modified resin B obtainedin Synthesis Example 2, and formation of line patterns, etching andobservation of line patterns before and after etching were conducted.

The formed pattern was dissolved to remove by conducting the removingtreatment in the same manner as in Example 7.

In case where post-baking was additionally conducted at 140° C. for 3minutes after development, the resist coating was also dissolved toremove by the same removing treatment.

Comparative Example 3

A photoresist composition was prepared in the same manner as in Example7 except for not adding the aniline modified resin. When formation ofline patterns, etching and observation of the form of line patternsbefore and after etching were conducted, there was observed seriousundercut. This undercut was unable to be prevented completely byadditionally conducting post-baking in the same manner as in Example 7after development.

Further, the formed line patterns were unable to be removed by theremoving treatment in the same manner as in Example 7. When period ofthe removing treatment was prolonged, the resist coating was removed ina peeling way, leaving undissolved photoresist residues floating.

Results of Examples 7 and 8 and Comparative Example 3 are tabulated inthe following Table 3.

TABLE 3 Form of Line Pattern Removability Before Etching *1 AfterEtching *2 of Resist not Not not Post-baking conducted Conductedconducted conducted conducted Conducted Example 7 ◯ ◯ Δ ◯ removable byRemovable by dissolution dissolution Example 8 ◯ ◯ Δ ◯ removable byRemovable by dissolution dissolution Comparative X Δ X Δ not Not Example3 removable by removable by dissolution dissolution *1 (Before etching)◯: with no pattern bite Δ: reduced pattern bite X: with pattern bite *2(After etching) ◯: with no pattern bite Δ: reduced pattern bite X: withpattern bite

Advantages of the Invention

The present invention provides a radiation-sensitive resin compositionwhich can form good pattern particularly with high adhesion to asubstrate and, when treated with a remover, can be easily removed not bypeeling but by dissolution.

Industrial utility

As has been described hereinbefore, the radiation-sensitive resincomposition of the present invention is preferably used as an etchingresist or the like in manufacturing semiconductor devices or liquidcrystal display.

What is claimed is:
 1. A negative-working radiation-sensitive resincomposition comprising an alkali-soluble resin, a cross-linking agentand an acid generating agent, wherein said alkali-soluble resin containsat least an alkali-soluble resin synthesized using as a monomercomponent a compound represented by the general formula (I):

wherein R represents a hydroxyl group or an alkyl group with 1 to 4carbon atoms, n is 0 or an integer of 1 to 3 and when n is 2 or 3, eachR group may be the same or different.
 2. A radiation-sensitive resincomposition according to claim 1, wherein the alkali-soluble resincontains an alkali-soluble resin obtained by polycondensation of thecompound represented by the general formula (I) and phenols with one ora mixture of two or more of aldehydes.
 3. A radiation-sensitive resincomposition according to claim 1, wherein the ratio of the compoundrepresented by the general formula (I) is in the range of 0.1 to 40% byweight in the total alkali-soluble resin.
 4. The radiation-sensitiveresin composition according to claim 1, further comprising a novolakresin.